CN1944384A - Coleus forskohlii extract main component and extracting method - Google Patents

Coleus forskohlii extract main component and extracting method Download PDF

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CN1944384A
CN1944384A CN 200610124900 CN200610124900A CN1944384A CN 1944384 A CN1944384 A CN 1944384A CN 200610124900 CN200610124900 CN 200610124900 CN 200610124900 A CN200610124900 A CN 200610124900A CN 1944384 A CN1944384 A CN 1944384A
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coleus forskohlii
acid
extract
acetone
coleus
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刘焱文
王晓明
吴和珍
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Hubei College of Chinese Medicine
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Abstract

The present invention is main components and extracting process of Coleus forskohlii extract. The main components in Coleus forskohlii extract are diterepene compounds, among which there are three monomers: Coleus forskohlii flower acid, Coleus forskohlii acid and Coleus forskohlii ketone. The extracting process of Coleus forskohlii extract includes the following steps: drying Coleus forskohlii herb, crushing, alcohol heating reflux extracting, vacuum concentrating to obtain extractum, mixing the extractum with silica gel, low pressure chromatographic separation in silica gel column, petroleum ether-acetone eluting, tumor cell inhibiting activity screening of the eluted components, further chromatographic separation in silica gel column, and Toyopearl HW-40F separating to purify and obtain compounds Coleus forskohlii flower acid, Coleus forskohlii acid and Coleus forskohlii ketone. The extract is used the material for antitumor Chinese medicine preparation.

Description

Coleus forskohlii extract main component and extracting method
Technical field
The present invention relates to a kind of extraction process of bulk drug, the structure of bulk drug main component and the application of bulk drug, specifically be to obtain extract and preparation technology from Coleus forskohlii Briq., the structure of 3 principal monomer compositions in the Coleus forskohlii extract is the purposes that bulk drug is made antitumor Chinese medicine preparation with the Coleus forskohlii extract.
Background technology
Coleus forskohlii Briq. (Coleus forskohlii (Wilid.) Briq.) is Labiatae (Labiatae) Coleus (Coleus Lour) plant.Perennial fragrant draft, tool tuberosity root, stem is upright, up to 60 centimetres.About 90 kinds of Coleus originates in India, grows in the India Plain and the Himalaya foot of the hill, is distributed in subtropics and area, temperate zone, comprises Nepal, Sri Lanka, Burma and East African province region-by-region.China has 6 kinds, is distributed in Yunnan, Guizhou, Fujian and Taiwan.Coleus forskohlii Briq. is common ornamental plant, in India, and cultivation in a large number, about 900～1000 tons of annual results.Use the stem cottage propagation spring to summer, like sunny or the part concealment, well-drained soil.Root, leaf are gathers autumn.Mainly acting as of Coleus forskohlii Briq. brings high blood pressure down, pain relieving, expansion bronchiole, vasodilation and cardiac stimulant.
In China, Coleus forskohlii Briq. records in " Chinese Plants will " 66 volumes, and " Yunnan Province's drug standard " (1987～1992) have been recorded its proterties and differentiated item.Its proterties is as follows: perennial perennial root, half meat draft, and rhizome is slightly cylindrical, and stem is sturdy, stem foot four prismatics, long 50～80 centimetres, 5～15 centimetres of diameters have branch estranged, and the long pubescence of being carried out is closeer on top, surperficial brown.Leaf is easily broken, and complete person is oval, the blunt or anxious point of tip, and blade base is downward to be wide wedge, edge tool knuckle-tooth, nearly meat, the two sides is close by fine hair, greyish-green.Wheel umbrella inflorescence is made up of 6～10 flowers, and majority is arranged in and reaches 11 centimetres raceme; Calyx is bell, is about 6 millimeters, the close villosity of throat's inner face, calyx tooth 5; The corolla hyacinthine, long 12～15 millimeters, outward by sparse gland point; Stamen 4, near overhanging or built-in, filigree heals into the sheath shape below the middle part.Seed big (thousand seed weight 1.3 grams), the pyrene circle is flattened shape, September at florescence.
The latter stage seventies, West Germany Hoechst India branch office extraction separation from Coleus forskohlii Briq. (Coleus forskohlii) goes out diterpene ester cpds Buddhist SCH (forskolin), confirms that after deliberation foskolin has good efficacy to heart failure, glaucoma, bronchial asthma.Activeconstituents forskolin has important medical functions, comprises hypotensively, and relaxing smooth muscle increases that Tiroidina is hormonal to be disengaged, and the secretion of promoting digestion road reduces intraocular pressure etc.India is used for the Digestive tract illness, as wind dispelling, go flatulence, control stomachache; Be used for recycle system illness, treatment congestive heart failure, coronary flow deficiency, improve cerebral blood circulation, separate painful effect, treatment asthma and trachitis.
1989 the end of the year China botanist just find subsequently it to be developed as a kind of new plant amedica---Coleus forskohlii Briq. oral liquid by this rare plant in Yunnan.Because this medicinal plant is evident in efficacy to bronchial asthma, Furen Pharmaceutical Co., Ltd., Hubei is new Chinese medicine---the coleus forskohlin capsule of treatment asthma with this product for the research of monarch drug in a prescription prescription again.In order to enlarge medicine resource, the said firm plans Coleus forskohlii Briq. and is transplanted to the Tongcheng County, Hubei Province, implements the GAP kind and plants.
The chemical research of Coleus forskohlii Briq. proves that it contains chemical ingredients and mainly contains compounds such as sesquiterpenoids, diterpenes, triterpenes, flavonoid and steroidal class.Pharmacological research proves that it has pharmacological action widely, as the spasmolysis of relievining asthma, and reduces the intraocular pressure effect, anticoagulant effect and antitumor action etc.
The comprehensive literature report, the diterpenes composition is the main component type of Coleus plant, a lot of diterpene-kind compounds have the important physical activity, such as, that Forskolin has is hypotensive, relaxing smooth muscle, increase Tiroidina hormonally disengage, promoting digestion road secretion and reduce the effect etc. of intraocular pressure, has been developed to new drug.And extract separates diterpene compound in the Coleus forskohlii Briq., has the potentiality and the purposes that are developed to new drug.
Summary of the invention
The object of the present invention is to provide and a kind ofly extract the bulk drug be used to prepare antitumor Chinese medicine preparation, the structure of the preparation technology of this bulk drug and 3 monomer components containing thereof from Coleus forskohlii Briq..
The technical scheme that realizes purpose of the present invention is:
A kind of extract that obtains from the Coleus forskohlii Briq. extraction, main component is a diterpene-kind compound, wherein three monomeric compounds are: one, Coleus forskohlii flower acid, chemical name is the 11-ketone group, 13-methyl, 8 (9), 13 (14) trans-Ladanum alkane-15-acid, white crystal, fusing point 158-160 ℃; Two, Coleus forskohlii acid, chemical name are the 11-hydroxyl, 13-methyl, 8 (9), 13 (14) trans-Ladanum alkane-15-acid, white crystal, fusing point 69-71 ℃; Three, Colexanthone, chemical name are 1-methoxyl group-3,5-dihydroxyl-7-methyl-mountain ketone, red crystals, fusing point 146-148 ℃; Extract quality content is 0.01%～0.3%.
The described extraction process step that obtains extract from Coleus forskohlii Briq. is:
Step 1, get the dry herb of Coleus forskohlii Briq., pulverizing, is that 95% alcohol heating reflux extracts three times with volumetric concentration, and three times amount of alcohol added is respectively 8 of the dry herb quality of Coleus forskohlii Briq., 6,4 times of amounts, three heating and refluxing extraction times are respectively 2,1,1 hour, united extraction liquid, concentrating under reduced pressure gets medicinal extract;
Step 2, medicinal extract and silica gel that step 1 is obtained are mixed by mass ratio at 1: 1.2, join the silicagel column upper end, carry out low-pressure column chromatography and separate, sherwood oil-acetone gradient elution, earlier use the sherwood oil wash-out, use the mixed solution gradient elution of sherwood oil and acetone again, its mixed solution PetroChina Company Limited. ether and the score of acetone volume are not 9: 1,8: 2,7: 3,6: 4,5: 5, use acetone then, ethanol gradient elution;
Step 3, step 2 wash-out stream part is suppressed the activity of tumor cells screening, filtering out antitumor active site, mainly to concentrate on sherwood oil and acetone mixeding liquid volume ratio be stream part of 8: 2;
Step 4, sherwood oil and acetone mixeding liquid volume ratio that step 3 is filtered out are stream part of 8: 2, further separate with silica gel column chromatography, and in conjunction with acrylate type polymer (Toyopearl HW-40F) separating for several times purifying, obtain Coleus forskohlii flower acid, three monomeric compounds of Coleus forskohlii acid and Colexanthone.
The extract that the present invention obtains from Coleus forskohlii Briq. has potentiality and the purposes that is developed to new drug, is used to prepare the bulk drug of antitumor Chinese medicine preparation.
Description of drawings
Fig. 1 is the process flow sheet of Coleus forskohlii Briq. extraction and separation and Extraction thing;
Fig. 2 is Coleus forskohlii flower acid (Coleonic Acid) 11-ketone group, 13-methyl, the molecular structural formula of 8 (9), 13 (14) trans-Ladanum alkane-15-acid [11-one, 13-methyl, 8 (9), 13 (14) Z-labdadien-15-acid];
Fig. 3 is Coleus forskohlii acid (Coleolic Acid) 11-hydroxyl, 13-methyl, the molecular structural formula of 8 (9), 13 (14) trans-Ladanum alkane-15-acid [11-ol, 13-methyl, 8 (9), 13 (14) Z-labdadien-15-acid];
Fig. 4 is Colexanthone (Colexanthone): 1-methoxyl group-3, the molecular structural formula of 5-dihydroxyl-7-methyl-mountain ketone [1-oxymethyl-3,5dihydroxyl-7-methyl xanthone].
The explanation of Fig. 1 process flow sheet
Getting the dry herb of Coleus forskohlii Briq., pulverize, is that 95% alcohol heating reflux extracts 3 times with volumetric concentration, and No. 3 times extracting solution merges, and is evaporated to small volume, reclaim, medicinal extract; Behind medicinal extract that obtains and the silica gel mix, carry out silica gel chromatographic column and separate, sherwood oil-acetone gradient elution is used earlier the sherwood oil wash-out, use the mixed solution wash-out of sherwood oil and acetone again, its mixed solution PetroChina Company Limited. ether and the score of acetone volume are not 9: 1,8: 2, and 7: 3,6: 4,5: 5, use acetone then, ethanol gradient elution; Wash-out stream part is suppressed the activity of tumor cells screening, filter out sherwood oil and acetone mixeding liquid volume ratio and be stream part of 8: 2, further separate with silica gel column chromatography, and in conjunction with Toyopearl HW-40F (acrylate type polymer) separating for several times purifying, separate and obtain Coleus forskohlii flower acid (1), (3) three monomeric compounds of Coleus forskohlii acid (2) and Colexanthone.
Embodiment
Embodiment 1:
Technical process extraction separation from Coleus forskohlii Briq. by Fig. 1 obtains Coleus forskohlii flower acid, three monomeric compounds of Coleus forskohlii acid and Colexanthone.
Extraction and separating technology step are:
Step 1, get 20 kilograms of the dry herbs of Coleus forskohlii Briq., pulverizing, is that 95% alcohol heating reflux extracts three times with volumetric concentration, and three times amount of alcohol added is respectively 8 of the dry herb quality of Coleus forskohlii Briq., 6,4 times of amounts, three heating and refluxing extraction times are respectively 2,1,1 hour, united extraction liquid, concentrating under reduced pressure gets medicinal extract 220 grams;
Step 2, medicinal extract 220 grams that obtain with step 1 are mixed thoroughly by 1: 1.2 mass ratio with silica gel, join 2000 gram silicagel columns upper ends, carry out low-pressure column chromatography and separate, sherwood oil-acetone gradient elution, earlier use the sherwood oil wash-out, use the mixed solution wash-out of sherwood oil and acetone again, its mixed solution PetroChina Company Limited. ether and the score of acetone volume are not 9: 1,8: 2,7: 3,6: 4,5: 5, use acetone then, ethanol gradient elution;
Step 3, step 2 wash-out stream part is suppressed the activity of tumor cells screening, filtering out antitumor active site, mainly to concentrate on sherwood oil and acetone volume ratio be stream part of 8: 2;
Stream part that step 4, the sherwood oil that step 3 is filtered out and acetone volume ratio are 8: 2, further separate with silica gel column chromatography, and in conjunction with Toyopearl HW-40F (acrylate type polymer) separating for several times purifying, separate obtain 30 milligrams of Coleus forskohlii flower acids, 20 milligrams of Coleus forskohlii acids, 10 milligrams of Colexanthones;
The Coleus forskohlii Briq. of gained is got the thing Coleus forskohlii flower acid, three monomeric compounds of Coleus forskohlii acid and Colexanthone, and its physics and chemistry characterizes as follows:
1. Coleus forskohlii flower acid compound (Coleonic Acid), molecular structural formula (referring to accompanying drawing 2) name: 11-ketone group, 13-methyl, 8 (9), 13 (14) trans-Ladanum alkane-15-acid
11-one，13-methyl，8(9)，13(14)Z-labdadien-15-acid(1)
White crystal, fusing point 158-160 ℃ (methyl alcohol);
IR brand (KBr): 3100,2959,1718,1631,1597,1451,1389,1375,1338,1321,1212,1138,864,678 centimetres -1
1H-NMR (600MHz, CD 3Cl) and 13C-NMR (150MHz, CD 3Cl): see Table 1;
EIMSm/z：
318[M](26)，301(35)，290(15)，285(12)，258(13)，219(7)，205(100)，195(17)，177(32)，163(23)，149(27)，135(97)，123(52)，121(39)，105(29)，91(38)，79(22)，69(29)，55(31)；
HREI-MS m/z：318.2188[M]，Calc.for C 20H 30O 3.318.2195。
Table 1 ColeonicAcid (1) 1H-NMR and 13The CNMR data
No. δ H，J(Hz) δ C 1 No δ H，J(Hz) δ C
1. 2. 3. 4. 5. 6. 7. 8. 9. 1.40(t)(3.0，12.6) 1.93(d)(12.6) 1.61(d)(3.6，10.8) 1.25(t)(4.2，13.2) 1.50(d)(13.2) 1.72(d)(14.4) 2.39(m) 2.52(d)(18.0) 2.35(m) 35.80 18.53 41.17 33.10 50.20 35.17 27.62 130.52 166.34 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 2.35(m) 5.76(s) 2.24(s) 1.78(s) 0.90(s) 0.93(s) 1.10(s) 40.98 200.26 39.77 161.75 115.28 171.69 19.13 11.44 32.48 21.28 18.11
2. Coleus forskohlii acid compound (Coleolic Acid), molecular structural formula (referring to accompanying drawing 3) name: 11-hydroxyl, 13-methyl, 8 (9), 13 (14) trans-Ladanum alkane-15-acid
11-ol，13-methyl，8(9)，13(14)Z-labdadien-15-acid(2)
White crystal, fusing point 69-71 ℃ (MeOH);
IR brand (KBr): 3362,2937,1721,1696,1648,1464,1440,1374,1242,1160,1125,1042,882 centimetres -1
1H-NMR (600MHz, CD 3Cl) and 13C-NMR (150MHz, CD 3Cl): see Table 2;
EIMSm/z：
320[M](5)，301(4)，287(3)，259(3)，231(6)，205(100)，191(15)，163(19)，149(50)，135(33)，121(36)，109(63)，95(34)，93(22)，81(18)，69(41)，67(17)，55(34)；
HREIMS m/z 320.2328[M]Calc.for：C 20H 32O 3320.2351。
Table 2 Coleolic Acid (2) 1H-NMR and 13C NMR data
No. δ C δ H，J(Hz) δ C 2 No. δ H，J(Hz)
1 2 3 4 1.82(d)(12.6) 1.49(m) 1.42(m)(13.2) 37.41 18.88 41.50 33.23 5 6 7 1.20(m)(3.6，7.2) 2.36(d)(3.6) 2.30(t)(9.6，2.4) 51.35 33.66 33.87
8 9 10 11 12 13 14 4.20(q)(4.2.10.8) 1.49(m) 6.08(s) 133.07 135.49 39.37 74.76 18.86 163.68 112.86 15 16 17 18 19 20 2.19(d)(0.6) 1.66(s) 0.85(s) 0.91(s) 0.99(s) 171.79 15.61 21.04 21.69 33.31 20.15
3. Colexanthone compound (Colexanthone) molecular structural formula (referring to accompanying drawing 4) name: 1-methoxyl group-3,5-dihydroxyl-7-methyl-mountain ketone
1-oxymethyl-3，5dihydroxyl-7-methyl xanthone(3)
Red crystals, fusing point 146-148 ℃;
1H NMR (600MHz, CD 3Cl+DMSO-d6): and 13C NMR (150MHz, CD 3Cl): see Table 3;
EIMSm/z：
272[M](100)，243(34)，242(18)，229(10)，213(7)，201(20)，199(16)，184(7)，171(11)，155(5)，136(7)，127(8)，115(14)，69(15)；
HREIMS m/z：272.0683[M]：Calc.for C 15H 12O 5，.272.0685。
Table 3 Colexanthone (3) 1H NMR, 13C-NMR, DEPT and HMBC data
No. δ H，J(Hz) δ C DEPT HMBC observed(C to H)
1. 2. 3. 4. 4a 4b 5. 6. 7. 8. 8a 9. 9a Me OMe OH 6.51(d)(2.4) 6.71(d)(2.4) 6.73(d)(2.4) 7.24(d)(2.4) 2.78(s) 3.92(s) 11.97s 164.89 98.36 98.03 101.58 157.87 152.33 164.27 117.17 108.89 103.25 137.68 165.71 137.51 24.98 55.02 ＝C ＝CH ＝C ＝CH ＝C ＝C ＝C ＝CH ＝C ＝CH ＝C O＝C ＝C CH3 CH3 OH OMe H-2 H-4 H-6 OH. Me Me，H-6，H-8 Me.H-6 Me H-2 H-6 OH

Claims (3)

1, a kind of extract that obtains from Coleus forskohlii Briq. is characterized in that, main component is a diterpene-kind compound, and wherein three monomers are: one, Coleus forskohlii flower acid, chemical name is the 11-ketone group, 13-methyl, 8 (9), 13 (14) trans-Ladanum alkane-15-acid, white crystal, fusing point 158-160 ℃; Two, Coleus forskohlii acid, chemical name are the 11-hydroxyl, 13-methyl, 8 (9), 13 (14) trans-Ladanum alkane-15-acid, white crystal, fusing point 69-71 ℃; Three, Colexanthone, chemical name are 1-methoxyl group-3,5-dihydroxyl-7-methyl-mountain ketone, red crystals, fusing point 146-148 ℃; Extract quality content is 0.01～0.3%.
2, the extraction and separation process of the described extract of claim 1 is characterized in that, the extraction separation step is:
Step 1, get the dry herb of Coleus forskohlii Briq., pulverizing, is that 95% alcohol heating reflux extracts three times with volumetric concentration, and three times the alcoholic acid add-on is respectively 8 of the dry herb quality of Coleus forskohlii Briq., 6,4 times of amounts, three heating and refluxing extraction times are respectively 2,1,1 hour, united extraction liquid, concentrating under reduced pressure gets medicinal extract;
Step 2, the medicinal extract and the silica gel that obtain with step 1 are mixed by mass ratio at 1: 1.2, join the silicagel column upper end, carry out low-pressure column chromatography and separate, sherwood oil-acetone gradient elution, earlier use the sherwood oil wash-out, use the mixed solution gradient elution of sherwood oil and acetone again, its mixed solution PetroChina Company Limited. ether and the score of acetone volume are not 9: 1,8: 2,7: 3,6: 4,5: 5, use acetone then, ethanol gradient elution;
Step 3, wash-out stream part is suppressed the activity of tumor cells screening, and filtering out antitumor active site, mainly to concentrate on sherwood oil and acetone mixeding liquid volume ratio be stream part of 8: 2;
Step 4, be stream part of 8: 2, further separate, and in conjunction with acrylate type polymer separating for several times purifying, obtain Coleus forskohlii flower acid, three monomeric compounds of Coleus forskohlii acid and Colexanthone with silica gel column chromatography to sherwood oil and the acetone mixeding liquid volume ratio that filters out.
3, the application of the described extract of claim 1 is characterized in that, as the bulk drug of the antitumor Chinese medicine preparation of preparation.
CN 200610124900 2006-10-31 2006-10-31 Coleus forskohlii extract main component and extracting method Pending CN1944384A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102366464A (en) * 2011-11-14 2012-03-07 范圣刚 Antitumor traditional Chinese medicinal composition
CN102746259A (en) * 2012-06-04 2012-10-24 中山大学 Labdane diterpenoid compounds, arborvitae seed extract, preparation method thereof and application thereof
CN103553919A (en) * 2013-11-05 2014-02-05 成都中医药大学 Terpenoid and preparation method and application thereof
CN103588745A (en) * 2013-11-26 2014-02-19 陕西嘉禾植物化工有限责任公司 Method for extracting and separating forskolin in coleus forskohlii

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102366464A (en) * 2011-11-14 2012-03-07 范圣刚 Antitumor traditional Chinese medicinal composition
CN102366464B (en) * 2011-11-14 2014-02-12 范圣刚 Antitumor traditional Chinese medicine composition
CN102746259A (en) * 2012-06-04 2012-10-24 中山大学 Labdane diterpenoid compounds, arborvitae seed extract, preparation method thereof and application thereof
CN103553919A (en) * 2013-11-05 2014-02-05 成都中医药大学 Terpenoid and preparation method and application thereof
CN103553919B (en) * 2013-11-05 2014-12-31 成都中医药大学 Terpenoid and preparation method and application thereof
CN103588745A (en) * 2013-11-26 2014-02-19 陕西嘉禾植物化工有限责任公司 Method for extracting and separating forskolin in coleus forskohlii
CN103588745B (en) * 2013-11-26 2015-10-28 陕西嘉禾植物化工有限责任公司 A kind of method of Extraction and separation not this Kelin from Coleus forskohlii Briq.

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